Di(3-thienyl)methanol → Di(3-thienyl)methanone

HRID 2115203Notes

Reaction equation

HRID 2115203 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[OH:7])=[CH:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[S:1]1[CH:5]=[CH:4][C:3]([C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[O:7])=[CH:2]1

Participants

4

Reactant 2

HCID 288490Di(3-thienyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 573773Di(3-thienyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.1 gm (10.7 mmol) of Di-thiophen-3-yl-methanol in 50 mL of dichloromethane at room temperature was added 3.0 gm (13.9 mmol) of PCC. The reaction suspension was allowed to stir 2 hrs at room temperature. After 2 hrs, the reaction mixture was filtered and precipitates were washed with dichloromethane. The combined filtrates were concentrated. The concentrated sample was purified by flashy chromatography (hexane:ethyl acetate, from 11 to 18% ethyl acetate over 16 column volume) to obtain 1.83 gm (88.0%) of light yellow crystals; 1H NMR 500 MHz (CDCl3) δ 8.02 (d, 1H), 8.01 (d, 1H), 7.62 (d, 1H), 7.61 (d, 1H), 7.40 (d, 1H), 7.38 (d, 1H).

Workup

  1. waitAfter 2 hrs
  2. filtrationthe reaction mixture was filtered
  3. customprecipitates
  4. washwere washed with dichloromethane
  5. concentrationThe combined filtrates were concentrated
  6. customThe concentrated sample was purified by flashy chromatography (hexane:ethyl acetate, from 11 to 18% ethyl acetate over 16 column volume)
  7. customto obtain 1.83 gm (88.0%) of light yellow crystals

Sources & evidence

ORD record
ord-75425183eb354c81a770cf9fa6f8368a
Source dataset
uspto-grants-2008_10
Patent number
US07435822B2

Reaction notes

Loading…